4-methyl-2-benzofuran-1,3-dione

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2-[1-(3-Ethoxy-4-methoxyphenyl)-2-methylsulfonylethyl]-4-methylisoindoline-1,3-dione was prepared by the procedure of Example 8 from 1-(3-ethoxy-4-methoxyphenyl)-2-methylsulfonylethylamine (1.4 g, 5.0 mmol) and 3-methylphthalic anhydride (810 mg, 5.0 mmol) in acetic acid (15 mL) to afford 2-[1-(3-ethoxy-4-methoxyphenyl)-2-methylsulfonylethylamine (1.0 g, 3.7 mmol) and 3-methylphthalic anhydride (590 mg, 3.7 mmol). The product was obtained as a white solid (1.78 g, 85% yield); mp, 143.0-145.0° C.; 1H NMR (CDCl3) δ 1.46 (t, J=7.0 Hz, 3H, CH3), 2.67 (s, 3H, CH3), 2.83 (s, 3H, CH3), 3.79 (dd, J=4.8, 14.5 Hz, 1H, CHH), 3.85 (s, CH, CH3), 4.11 (q, J=7.0 Hz, 2H, CH2), 4.54 (dd, J=9.8, 14.5 Hz, 1H, CHH), 5.89 (dd, J=4.8, 9.9 Hz, 1H, NCH), 6.81-6.85 (m, 1H, Ar), 7.65 (d, J=7.5 Hz, 1H, Ar); 13C NMR (CDCl3) δ 14.65, 17.54, 41.49, 48.63, 54.89, 55.89, 64.44, 111.36, 112.48, 120.44, 121.17, 128.24, 129.69, 132.00, 133.69, 136.63, 138.29, 148.51, 149.55, 167.99, 168.46; Anal Calcd for C21H23NO6S: C, 60.42; H, 5.55; N, 3.36. Found: C, 60.68; H, 5.40; N, 3.15.

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 2,6-dioxo-3-benzyloxycarbonylamino-5-acetoxypiperidine (9 g, 28.2 mmol) (U. Teubert et al, Arch. Pharm. Pharm. Med. Chem. (1998) 7-12), and Pd/C (10%, 0.9 g) in acetic acid (90 mL) is shaken under hydrogen (50-60 psi) for 3 hours. The suspension is filtered through a pad of Celite and washed with acetic acid. To the filtrate is added 3-methylphthalic anhydride (4.56 g, 28.2 mmol) and this mixture is heated at reflux for 18 hours. The solvent is removed in vacuo to give 3-(4-methyl-1,3-dioxoisoindolin-2-yl)-2,6-dioxo-5-acetoxypiperidine which can be further purified by column chromatography. The suspension is filtered through a pad of Celite washed with acetic acid this mixture is heated at reflux for 18 hours The solvent is removed in vacuo

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 3-Amino-1-ethylpiperidine and 3-methylphthalic anhydride are reacted in a similar manner so that described in Example 3 to give the title compound.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 3-Amino-1-ethylpiperidine and 3-methylphthalic anhydride are reacted in a similar manner so that described in Example 3 to give the title compound.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 2,6-dioxo-3-benzyloxycarbonylamino-5-acetoxypiperidine (9 g, 28.2 mmol) (U. Teubert et al, Arch. Pharm. Pharm. Med. Chem. (1998) 7–12) and Pd/C (10%, 0.9 g) in acetic acid (90 mL) is shaken under hydrogen (50–60 psi) for 3 hours. The suspension is filtered through a pad of Celite and washed with acetic acid. To the filtrate is added 3-methylphthalic anhydride (4.56 g, 28.2 mmol) and this mixture is heated at reflux for 18 hours. The solvent is removed in vacuo to give 3-(4-methyl-1,3-dioxoisoindolin-2-yl)-2,6-dioxo-5-acetoxypiperidine which can be further purified by column chromatography. The suspension is filtered through a pad of Celite washed with acetic acid this mixture is heated at reflux for 18 hours The solvent is removed in vacuo